


Wait For It

by RubberDuckSoup



Category: Supernatural
Genre: Abusive John Winchester, Angst and Fluff and Smut, Bad Parent John Winchester, Bisexual Dean Winchester, Castiel/Dean Winchester First Kiss, Dean Winchester in Denial, Dean Winchester is Bad at Feelings, Dean Winchester is Repressed, Homophobic John Winchester, Internalized Homophobia, John Winchester Being an Asshole, M/M, Story within a Story, Storytelling, Trauma
Language: English
Status: Completed
Published: 2020-04-19
Updated: 2020-04-19
Packaged: 2021-03-02 04:01:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,922
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23738770
Author URL: https://archiveofourown.org/users/RubberDuckSoup/pseuds/RubberDuckSoup
Summary: Dean tells a story from his past. Cas has questions.
Relationships: Castiel/Dean Winchester, Dean Winchester/Original Male Character(s)
Comments: 4
Kudos: 222





	Wait For It

**Author's Note:**

> Content warnings. This features John Winchester being abusive, homophobic, and the worst. The only sex happens within the story that Dean tells but it does get explicit.

“Dean Winchester?” asks a man standing in front of their table. Dean blinks up at him. He’s tall, nearly as tall as Sam. He has dark eyes and salt and pepper hair long enough to push behind his ears. Dean squints, trying to picture him without the beard and minus a couple of decades.

“Holy shit! Jeremiah!” He stands and flounders for a second before offering the taller man his hand. Jeremiah takes it and pulls him into a back-slapping hug.

Sam clear his throat. Dean turns back to the booth. “Guys, this is an old friend, Jeremiah Sloane. Jeremiah, this is Jack, Castiel, and my brother Sam.” Sam stands and shakes his hand.

“ _This_ is Little Brother Sam?” Sam has about half an inch on him.

“Yeah, he’s a giant. Don’t make a deal of it. His head is big enough as it is.”

Sam rolls his eyes. “How do you guys know each other?”

“Dad and I worked with him about twenty years ago. He’s a hunter.”

“Was a hunter,” Jeremiah corrects. “Gave it up when I got married.”

“You guys should catch up. Why don’t you join us?” Sam offers.

“We’ve already ordered,” Cas says from his spot in the booth. Dean shoots him a glare. _Rude_.

“I just came in for a drink before heading home.”

“Perfect, how about I buy you one?” Dean guides Jeremiah to a couple of barstools toward the end of the bar. Probably shouldn’t have an audience for this conversation. “I can’t believe we just ran into you.” He shakes his head.

“You didn’t. I may not be a hunter anymore but I still have connections. I heard you were working a case in the area and I asked a friend at the sheriff’s office to keep an eye out for a vintage Impala.”

“You were looking for me?” Dean doesn’t know how to feel about that.

“I wanted to— I never liked how we left things. I did look for you the next morning but you were already gone. I didn’t want to make things worse with your dad but I should’ve tried to find you.”

Dean bristles and shifts on the stool. “No. You shouldn’t have. You were right, it would’ve made it worse. It wasn’t your mess to clean up. Anyway, that was a long time ago. It’s water under the bridge. I’m doing fine.”

“That’s good to hear. You’re still hunting?”

“Wouldn’t know what to do with myself if I weren’t.”

“I know what you mean. I had a long adjustment period after I stopped. Working regular hours, sleeping at least seven hours a night, it felt so alien. Now I couldn’t go back to that life if I tried. Wouldn’t want to either. I am as settled as they come.” He fiddles with his wedding band. “Ten years this March.”

“Good for you, man.” Dean clinks his beer bottle against Jeremiah's glass. “See? We’re both in good places.”

“I guess so. I should go. I was telling the truth, I did only have time for a drink. Max worries if I get home too late. It was good to see you.” He gets up to go.

“You too.” Dean watches him go, finishes his beer and returns to the table. After they’ve eaten and paid the bill they pile back into the Impala and continue the drive back to the bunker.

“Who was that man?” Cas asks after a few hours on the road.

“What?” Dean glances at the mirror to the backseat. Jack is asleep against the window but Cas is staring intently at him. Par for the course.

"The man at the bar. Who was he?"

“An old friend, like I said.”

“You’ve never mentioned him.”

“That’s true,” Sam agrees, coming out of a light doze in the passenger seat.

“What? I’m supposed to tell you about everyone I’ve ever met?”

“You usually do,” Sam says. “Most of the time I can’t get you to shut up but I never heard about this guy until today.”

“He was just another hunter Dad and I worked with while you were at Stanford.”

“Why were you so flustered when he first showed up?” Sam presses.

“I wasn’t flustered! I was just surprised. I hadn’t seen him in a long time and he was…” Dean trails off.

“An old friend?” Sam says, skeptical.

“Right, my old friend. Who I guess you could also call an Ex.” Dean is not sure why he was putting up such a fight about admitting to it and equally not sure why he’s caving now. He’s probably just tired. “You got me. I was surprised to see him because he was an old flame.”

“Seriously?” Sam looks at him, both brows raised.

“Yep.”

“Care to elaborate?”

“Nope.”

“Dean, you can’t just drop a bombshell like that and then clam up. What’s the story?”

“No story. I was twenty. He was twenty-two. Dad and I were taking out a string of vampire nests along the Ohio River. Jeremiah was a local hunter helping us out. He flirted with me and I flirted back. And eventually…”

“You flirted with him in front of Dad?” Sam asks, apparently, that’s the detail he’s having the most trouble grasping.

“Of course not in front of Dad.”

“Eventually?” Cas asks.

“What?”

“You said ‘And eventually.’ Eventually what?” Dean doesn’t even have to look in the rearview mirror to know he’s doing the ‘I don’t understand’ head-tilt.

“We’d finished off the last nest and I was full of adrenaline and I kissed him. Not in front of Dad.” He heads off Sam’s question. “Dad was calling Bobby looking for the next job. We kissed. Jeremiah slipped me his room key and so we…”

“You keep not finishing your sentences. It’s irritating,” Cas mutters. Dean sighs. He should know better than to expect Castiel to infer anything by now.

“We hooked up. I was twenty and horny and I hooked up with a guy, okay?” Dean didn’t mean to shout.

“Okay,” Jack mumbles and pulls his jacket over his face. “G’night.”

Sam is laughing way too hard.

“Shut up, Sam.”

“I didn’t say anything.” Sam takes a few deep breaths. “Let me guess, you snuck away while he was asleep and never saw him again until tonight?”

“No. Dad kicked in the door.”

“Shit.” Sam whistles.

“It was pretty funny. John Winchester charging in like Dirty Harry to protect my nonexistent virtue.”

“Heh.” Sam laughs because he’s Sam and he knows that’s the reaction Dean wants.

“I don’t see how that’s funny,” Cas says because he’s Cas.

Dean shrugs. “There, that’s the story of the only time I hooked up with a guy.”

“That was the only time?” Sam repeats.

“ _Yes_ , that was the only time. I got it out of my system. The end.”

“Okay.” Sam holds his hands up in surrender.

They get back to the bunker and go to their respective beds, Dean can’t sleep. Also par for the course. He goes to the kitchen and takes a beer from the fridge.

“Dean.”

Dean startles then curses at himself for startling. “Eleven years, Cas. Eleven years and you’re still doing the jump scare?” He turns to face the angel.

“You were the one who jumped.”

Dean chuckles. He doesn’t have it in him to stay mad at Cas for more than twenty seconds. “True. What can I do for you, buddy?”

“I want you to tell me what happened between you and Jeremiah.”

“I already told you.”

“I want you to tell me again. I think you were holding things back.”

“Yeah, well some details would be inappropriate to share with my brother. Not to mention Jack.”

“Neither of them are here now.”

“Okay,” Dean shakes his head. Of course, Cas won’t let it go that easily. “Where do you want me to start?”

“Why were you attracted to him?”

“Uh,” Dean can feel the heat rushing to his cheeks. “I don’t know. I was young. He was only two years older but he was manly in a way that I really wasn’t back then. I was scrawny and soft looking. I mean I could still kick serious ass but you wouldn’t know it by looking at me.” Dean had hated it. He was finally an adult, but no one took him seriously because he looked like he should be in a boy band. Hell, even his kid brother towered over him. “Jeremiah, he was big and muscular. And he had this jaw… And he had this way of looking at me like he knew what I was thinking. And _I_ didn’t even know what I was thinking. You know?” Dean laughs.

“No. I don’t know.” Cas shakes his head and Dean has to bite his tongue before they get into another debate about rhetorical questions.

“Right. Well, he flirted with me. Real subtle though. Legs brushing under the table, licking his lips while looking at mine. No man had ever done that to me before. But women had. I knew what it meant. I was confused. I liked it but it made me uncomfortable but I didn’t want it to stop.” Dean is staring down at the table, his hand massaging the back of his neck. He hasn’t thought about this in years. He’s worked very hard at not thinking about it.

“Anyway, we finished the hunt and Dad went to call Bobby and I was alone with Jeremiah. We said goodbye, maybe we’d see each other again sometime. I started walking away and he grabbed my arm. He had these big hands and a real firm grip and I spun around and I just kissed him. Right behind the motel where anyone coulda seen. When we pulled away he slipped something into my hand. His room key.

“That night I told Dad I was going to see a girl I’d met at the bar a few days ago. He didn’t mind if I went out as long as we weren’t on a job. He just told me to be back by checkout the next day because he had a lead on the next hunt. So I go to Jeremiah’s room. I told myself I wasn’t really going to do anything. I was just going to get some time away from Dad. Okay, maybe I’d kiss him again because that had been alright.

“I unlocked the door and he was sitting on the bed in just his jeans and he patted the spot next to him and…”

“And? You keep—“

“Not finishing my sentences, I know.” Dean laughs. “We kissed and rolled around on the bed and got each other's clothes off. At this point, I hadn’t done anything I wouldn’t do with a girl and I figured that’s where I should stop.”

“Did you stop?”

“I thought I was going to. Right up until I told him I wanted to suck his dick.” Dean laughs again, this time at himself. “Never did that with a girl. So he put on a condom and got up over my face and I —“ Dean covers his eyes, wincing at the memory. “This is so fucking embarrassing. I gagged so hard I almost puked. He pulled out. ‘You’ve never done this, huh?’ he says. And me, like an idiot, swears that I had only not with a man. Which makes no sense. Right?”

“Um,” Cas says, forehead furrowing. “ I suppose it could be possible under partic—-“

“No, no, Cas—“ Dean waves him off. “Rhetorical.” Dean takes a swig of his beer to get his breath back. “He knew what I meant and he went slow and kind of guided me like this.” Dean grabs a handful of his hair. “I got the hang of it. Fast learner, me.” He’s blushing again. He can’t believe he’s telling this to him. To anyone. Maybe because he’s a little drunk or maybe because it’s Cas or maybe just because he’s spent too long not telling it, he barrels on ahead. “Uh, so we keep going. He flips me over which made me kind of nervous because I really didn’t think I would go there the first time and also he’d just finished so how was he going to be able to anyway? But he actually starts uh… using his tongue.” He’d also told Dean he had a pretty ass, tight and sweet. But there are some things too intimate to divulge even to Cas.

“You enjoyed that?” Cas leans forward.

“Loved it. Thought I was in Heaven. And now that I’ve been to some actual Heavens it’s still up there. I think we would’ve gone even further but…”

“Your father kicked in the door.”

_What do you know? He inferred._

“Yeah,” Dean gulps. “I don’t know how he found out. Maybe someone saw us and tipped him off. Anyway, he yells “Dean, you’ve got five minutes to get dressed and get to the car.”

Dean shot to his feet and stood frozen to the spot until John pulled the splintered door closed. Then he fell onto the bed, shaking and crying. John hadn’t made him cry like that since the night Sammy left for school. He figured he was immune by then.

“Uh… I got dressed. Jeremiah told me I was an adult and I didn’t have to go with him if I didn’t want to.” He put an arm around Dean’s shoulders to comfort him but Dean brushed him off.

“But you went with him?”

“He was a bastard sometimes but he was my dad. My only family with Sam in exile. I wasn’t going to lose that for some guy I barely knew. I went out to the car and I told Dad it wasn’t what he thought. Except it was. It was exactly what he thought but I still tried to explain myself. I needed him to understand.” A tear rolls down his cheek. “I said ‘I still like girls but I guess I—“ That’s as far as I got before he backhanded me across the mouth.”

Cas shudders and reaches for Dean’s hand. Dean brings the bottle to his lips instead.

“'Not another word, boy!’” Dean growls in imitation. “‘Get in the damn car!’ I did. But Jeremiah had come running out of the motel, yelling ‘You can’t do that!’”

“What did your father do?”

“Shouted ‘Come near my kid again and I’ll end you.’ And drove us away. The next morning he says, ’Son, I thought you had more self-respect than that.’ Never brought it up again.” Dean lets out a weary breath.

“That was a cruel thing your father did,” Castiel says after a few minutes of silence.

“He didn’t hit me that hard. I got it worse the time Sammy ran away on my watch.”

“No, not that. That was wrong, of course. But not letting you tell him how you felt.”

“He was doing what he thought was right.” His idea of right was questionable but in his way, he was protecting his sons. Dean knows that. He’s made peace with it.

“He made you hide yourself from him. He made you hide from yourself.”

“No, he didn’t. There was nothing to hide from. It was just a dumb one-night-stand.”

“You stopped pursuing relationships with men because he didn’t approve.”

“It’s not that big of a deal, Cas. I was experimenting. I tried a lot of things on for size. That one didn’t fit.”

“I know how much your father’s opinion meant to you—

“Cas, stop. Maybe I would’ve done it a few more times if he hadn’t found out but I would’ve come to the same conclusion.”

“You said it was like Heaven.”

“It was sex,” Dean scoffs. “I know you haven’t had a lot of it but I shouldn’t have to explain that it feels good.” Dean gives him a suggestive eyebrow waggle. Sometimes the only way to make the angel drop something is to make him deeply uncomfortable. Cas frowns. _Mission accomplished._

“I’ve wondered for a long time why you were so scared of yourself.” _Mission not accomplished._ “I came up with many reasons.”

“Gee thanks, buddy.” Dean raises his bottle. Cas begins to pace.

“You have a lot of flaws. Anger issues, poor impulse control, you drink far too much.”

“Again, thanks.”

“But you had a literal monster inside of you and you overcame it. And you forgave yourself.”

“I don’t know about that,” Dean mutters.

“Yet you are still terrified of being something your father couldn’t accept.”

“I’m not afraid.” It would sound more convincing if he weren’t staring at the floor.

“No?”

“No.” Dean nods, his jaw tight.

“You haven't felt desire for a man since?”

Dean is prepared to deny it but he’s never been good at lying to Cas. “Desire is a broad word. Sure, I’ve wondered if someone would be a good kisser or what they look like naked or—point is, I’ve never wanted that again. Can we please drop it?”

“Alright.” Cas looks disappointed. It’s a too-familiar look and Dean really doesn’t like it.

“I’m sorry. I know you were trying to help.”

Cas nods, his lips pressed firmly together. 

“I…” Dean doesn’t know what else to say. He’s just staring at Cas in silence. Again. _Why is that always happening?_

“Good night, Dean.” Cas turns to go. Without thinking, Dean reaches out and grabs his bicep. Cas turns. Dean pulls him closer and they’re kissing.

“I may have to rescind a few things I—“ Dean starts but Cas shuts him up with another kiss.

**Author's Note:**

> Thanks for reading. I have watched Supernatural through season 14 but it's not one of my primary fandoms. Please forgive me for any timeline or continuity mistakes. This story wouldn't leave me alone until I wrote it. Comments and kudos are always welcome.


End file.
